高效铜催化不对称烷基化及其在赘生物毒素和病毒毒素全合成中的应用

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-12-26 DOI:10.1002/adsc.202401338

Guodu Liu, Lin Fan, Jiashan Li, Xinlong Yan, Zongwei Li, Yang Wang, Le Pan

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引用次数: 0

摘要

不对称烷基化反应是合成手性非天然α-取代α-氨基酸的重要方法之一。本文报道了Cu/(4S,2R)-tBu-Phosferrox催化剂催化的不对称烷基化反应。在负载低至1.0 mol %时，该催化剂在不对称烷基化反应中表现出最高的催化性能，产率高达95%，ee达99%，这是迄今为止最好的结果。此外，该方法还成功应用于非天然氨基酸4,5- oh - leu的规模化实际合成，可直接用于阴茎素、阴茎酸素等4种阴茎素毒素和6种病毒毒素的全合成。

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Efficient Cu-catalyzed Asymmetric Alkylation and Application in the Total Synthesis of Phallotoxins and Virotoxins

Asymmetric alkylation is one of the most important methods for synthesis of chiral unnatural α-substituted α-amino acids. Herein, we reported the asymmetric alkylation catalyzed by Cu/(4S,2R)-tBu-Phosferrox catalyst. This catalyst exhibits the highest catalytic performance in the asymmetric alkylation at catalyst loading as low as 1.0 mol %, giving the desired products with up to 95% yield and >99% ee, which is the best results to date. Furthermore, this method was successfully applied to the scalable practical synthesize of unnatural amino acid 4,5-OH-Leu, which could be directly used in the total syntheses of phalloidin, phallacidin, other four phallotoxins and six virotoxins.

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.